N-(Hydroxymethyl)phthalimide
[CAS# 118-29-6]

Identification

• Classification: API >> Nervous system medication >> Antidepressant, manic
• Name: N-(Hydroxymethyl)phthalimide
• Synonyms: 2-(Hydroxymethyl)-1H-isoindole-1,3(2H)-dione
• Molecular Formula: C₉H₇NO₃
• Molecular Weight: 177.16
• CAS Registry Number: 118-29-6
• EC Number: 204-241-4
• SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CO

Properties

• Melting point: 140-145 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

N-(Hydroxymethyl)phthalimide is a chemical compound with the molecular formula C9H7NO3. It is a derivative of phthalimide in which a hydroxymethyl group is attached to the nitrogen atom. Due to its unique reactivity and functional properties, this compound is of great importance in organic synthesis and various industrial applications.

N-(Hydroxymethyl)phthalimide was first synthesized in the early 20th century during the study of phthalimide derivatives and their potential applications. The driving factors for modifying phthalimide to include hydroxymethyl groups were the exploration of new functionalities and the improvement of the reactivity of phthalimide-based compounds.

The synthesis of N-(Hydroxymethyl)phthalimide involves the reaction of phthalimide with formaldehyde. The process is usually carried out in aqueous or alcoholic media, and a basic catalyst is usually used to promote the reaction. The reaction produces N-(Hydroxymethyl)phthalimide, which can be isolated and purified by crystallization or other separation techniques.

N-(Hydroxymethyl)phthalimide is a versatile reagent for organic synthesis. It can be used as a building block to introduce phthalimide moieties into various molecules. This feature is valuable in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. The hydroxymethyl group can also undergo further reactions, providing additional synthetic flexibility.

In the pharmaceutical industry, N-(hydroxymethyl)phthalimide is used to synthesize active pharmaceutical ingredients (APIs) and intermediates. Its reactivity and stability make it a useful precursor for the production of various pharmaceutical compounds. In addition, it can serve as a protecting group for amines, protecting them during multi-step synthetic processes.

N-(hydroxymethyl)phthalimide is used in polymer chemistry for the modification and functionalization of polymer backbones. It can introduce phthalimide groups into polymers, enhancing their thermal stability, mechanical properties, and resistance to degradation. This application is particularly useful in the development of advanced materials for coatings, adhesives, and electronic devices.

The agrochemical industry utilizes N-(hydroxymethyl)phthalimide to synthesize herbicides, fungicides, and insecticides. It serves as a precursor for bioactive compounds, which helps in the development of effective and environmentally friendly agricultural products.

In the research laboratory, N-(hydroxymethyl)phthalimide is an invaluable tool for exploring new chemical reactions and developing innovative synthetic methods. Its availability and versatility make it a workhorse reagent for chemists working at the forefront of every area of ​​chemistry.

References

2019. New relevant pesticide transformation products in groundwater detected using target and suspect screening for agricultural and urban micropollutants with LC-HRMS. Water Research.
DOI: 10.1016/j.watres.2019.114972

2007. Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides. Carbohydrate Research.
DOI: 10.1016/j.carres.2007.03.009

2001. Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-alpha-D-mannopyranosides. Carbohydrate Research.
DOI: 10.1016/s0008-6215(01)00088-x